That Guy: Tom McLeod


In order to succeed, one must be willing to fail. In a matter of minutes and several short stories later, Tom McLeod had taught one of life's greatest lessons. Most every success is preceded by failure. After all, failure is one of life's best teachers. In order to succeed, therefore, you must not be afraid of it. Tom sure wasn't seven years ago, when he took a leap of faith and passed a note to the cute freshman across class, asking her to lunch. And this June, he married that cute freshman.


Tom has not only created a successful career for himself, but he's created a successful life by surrounding himself with amazing people, which he says is the real secret. If you're looking for a great example of a man who truly enjoys life, look no further. Once a month, Tom invites his friends to spend an entire day with him at the movies. It's an enjoyable diversion, where everyone can disconnect. He's a man who indulges in his love of pickup basketball by searching the city for a court and people to play with, sometimes forming lasting friendships. Tom's also a big dreamer. He dreams of the day his milk and deli ham communicate with his phone. Need to know what to pick up at the store? No need to open the fridge, just check your phone! Tom is a man who's found success in life by enjoying every day.

If you could describe yourself in three words, what would those words be?

Kind, Observant, Comfortable.

Tell us about a girl in your life who rocks.

My wife and mother obviously rock, so they're off limits. My good friend Rebekah Iliff rocks for sure. She's run various businesses, is currently branching out into a new startup, and always has time to discuss a good book. Her ability to crush it in business, always be there for her friends, and maintain her feminine mystique prove over and over that she's a girl who rocks.

What are your dreams/goals/ambitions?

I'd love to have a happy and healthy family that gets a leg up on their own success from my hard work. Also, I'm down to be president.

What are you most proud of?

Making rent every month while never having a boss.

What do you find most sexy about a girl?

Probably laughing at my jokes. Less about the laughter, more about the smiles.

Where do you see yourself in 10 years?

Hopefully investing in the futures of people like me right now and hopefully dancing my face off somewhere warm.

What is the number one item on your bucket list?

I want to go to space. It's a cliché, but space!

Who has been the biggest male influence in your life and why?

It was my father hands down. He was the biggest influence because he was always there. So now that he's not, I have a lot of points of reference to reflect upon when making decisions.

What is the biggest risk you've ever taken and what did you learn from it?

I never really feel like I take risks. I generally have a plan and an exit. I imagine what I've learned from risky behavior is to always have an exit.

What is one stereotype about men that isn't really true?

That we don't like assertive women. I think almost every guy I know loves assertive women. We just don't like inflexible people.

*Interview conducted and compiled by Lauren Rhew* 

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